Processes for preparing conjugated linoleic acid from conjugated linoleic acid esters

Abstract

Processes for preparing conjugated linoleic acid are described wherein a conjugated linoleic acid lower alkyl ester is subjected to hydrolysis in the presence of an enzyme to form a hydrolyzate comprising a conjugated linoleic acid and a lower alkanol, wherein at least a portion of the lower alkanol is continuously removed; the hydrolyzate is separated into an organic phase and an aqueous/alcoholic phase; and the conjugated linoleic acid is separated from the organic phase.

1. A process comprising:
 (a) subjecting a conjugated linoleic acid lower alkyl ester to hydrolysis in the presence of an enzyme to form a hydrolyzate comprising a conjugated linoleic acid and a lower alkanol, wherein at least a portion of the lower alkanol is continuously removed; 
 (b) separating the hydrolyzate into an organic phase and an aqueous/alcoholic phase; and 
 (c) separating the conjugated linoleic acid from the organic phase. 
 
     
     
       2. The process according to  claim 1 , wherein the conjugated linoleic acid corresponds to the general formula (I):
   R 1 CO—OR 2   (I) 
 
       wherein R 1 CO represents a linoleic acid acyl group having conjugated double bonds and R 2  represents an alkyl group having from 1 to 4 carbons. 
     
     
       3. The process according to  claim 1 , wherein the enzyme comprises a compound selected from the group consisting of esterases, lipases and mixtures thereof. 
     
     
       4. The process according to  claim 1 , wherein the enzyme comprises at least one microorganism selected from the group consisting of  Alcaligenes., Aspergillus niger, Candida antarctica  A,  Candida antarctica  B,  Candida cylindracea, Chromobacterium viscosum, Rhizomucor miehei, Penicilium camemberti, Penicilium roqueforti, Porcine pancreas, Pseudomonas cepacia, Pseudomonas fluorescens, Rhizopus javanicus, Rhizopus oryzae , and  Thermoinyces lanugenosus.    
     
     
       5. The process according to  claim 2 , wherein the enzyme comprises at least one microorganism selected from the group consisting of  Alcaligenes., Aspergillus niger, Candida antarctica  A,  Candida antarctica  B,  Candida cylindracea, Chromobacterium viscosum, Rhizomucor miehei, Penicilium camemberti, Penicilium roqueforti, Porcine pancreas, Pseudomonas cepacia, Pseudomonas flucrescens, Rhizopus javanicus, Rhizopus oryzae , and  Thermomyces lanugenosus.    
     
     
       6. The process according to  claim 1 , wherein the enzyme comprises at least one microorganism selected from the group consisting of  Candida antarctica  B,  Chromobacterium viscosum , and  Thermomyces lanugenosus.    
     
     
       7. The process according to  claim 2 , wherein the enzyme comprises at least one microorganism selected from the group consisting of  Candida antarctica  B,  Chromobacterium viscosum , and  Thermomyces lanugenosus.    
     
     
       8. The process according to  claim 1 , wherein the hydrolysis is carried out at a temperature of from 20 to 80° C. 
     
     
       9. The process according to  claim 2 , wherein the hydrolysis is carried out at a temperature of from 20 to 80° C. 
     
     
       10. The process according to  claim 6 , wherein the hydrolysis is carried out at a temperature of from 20 to 80° C. 
     
     
       11. The process according to  claim 7 , wherein the hydrolysis is carried out at a temperature of from 20 to 80° C. 
     
     
       12. The process according to  claim 1 , wherein the hydrolysis is carried out to a conversion of 60% by weight. 
     
     
       13. The process according to  claim 1 , wherein a constant water content of from 30 to 70% by weight is maintained during the hydrolysis and at least a portion of the water/lower alkanol phase is continuously removed by application of a vacuum of from 20 to 60±5 mbar. 
     
     
       14. The process according to  claim 1 , wherein water content is adjusted to from 0 to 20% by weight during the hydrolysis and at least a portion of the water/lower alkanol phase is continuously removed by application of a vacuum of from 20 to 60±5 mbar. 
     
     
       15. The process according to  claim 1 , wherein the hydrolysis is carried out in two or more stages and a water content of from 50 to 75% by weight is used in each stage. 
     
     
       16. The process according to  claim 1 , wherein the hydrolysis is carried out to a conversion of greater than 90% by weight. 
     
     
       17. The process according to  claim 1 , wherein the hydrolysis is carried out to a conversion of greater than 99% by weight.